Acetaldehyde → N-(2-(3-methoxyphenyl)ethyl)-4-(2-(1-hydroxyethyl)-5-methoxybenzyl)piperidine

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Reaction Steps

A solution of N-(2-(3-methoxyphenyl)ethyl)-4-(2-bromo-5-methoxybenzyl)piperidine (the compound of Example 64) (500 mg, 1.2 mmol) in tetrahydrofuran (5 ml) was cooled to −78° C., and n-butyllithium (a 1.57M hexane solution, 910 μl, 1.4 mmol) was added dropwise thereto. After the resulting solution was stirred at the same temperature for 30 minutes, acetaldehyde (135 μl, 2.4 mmol) was added dropwise thereto, and the reaction mixture was stirred at the same temperature for another 1 hour. A saturated aqueous sodium hydrogencarbonate solution was added thereto and the resulting mixture was slowly heated to room temperature. Then, the mixture was extracted with ethyl acetate and the combined extract layer was washed with a saturated aqueous sodium chloride solution. After drying over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and the residue was purified by a silica gel column chromatography (chloroform/methanol=30/1 to 10/1) to obtain the title compound (386 mg, 84%) as a brown oil.

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